Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-β-carboline formation

被引:16
作者
Brandt, Simon D.
Mansell, David
Freeman, Sally
Fleet, Ian A.
Alder, John F.
机构
[1] Univ Manchester, Sch Chem Engn & Analyt Sci, Manchester M60 1QD, Lancs, England
[2] Liverpool John Moores Univ, Sch Pharm & Chem, Liverpool L3 3AF, Merseyside, England
[3] Univ Manchester, Sch Pharm & Pharmaceut Sci, Manchester M13 9PL, Lancs, England
关键词
tryptamines; hallucinogens; decarboxylation; forensic; fingerprint; tetrahydro-beta-carbolines; synthesis; biological activities; analytical chemistry;
D O I
10.1016/j.jpba.2006.02.007
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
N-Alkylated tryptamines have complex psychoactive properties. Routes for clandestine synthesis are described on Internet websites one of which involves the thermolytic decarboxylation of tryptophan to tryptamine as a precursor to psychoactive compounds. High boiling solvents and ketone catalysts have been employed to facilitate the decarboxylation of tryptophan. The present study has revealed that there is formation of tetrahydro-p-carboline (THBC) derivatives which may originate from reaction with both the solvent and the ketone catalyst. The application of gas chromatography electron- and chemical-ionisation ion trap tandem mass spectrometry (GC-IT-MS-MS), in combination with nuclear magnetic resonance (NMR), led to the isolation and identification of 1,1-disubstituted-tetrahydro-p-carbolines formed as major impurities in the tryptamine. Confirmation was by synthesis of the THBC derivatives from tryptamine using Pictet-Spengler cyclisation. Under El-conditions, mass spectral characterisation of the THBCs suggests predominance of alkyl cleavage. These impurities will yield a useful profile for identification of the synthetic pathway and likely reagents employed, particularly a "fingerprint" of the ketone catalyst and an insight into the influence of solvents and catalysts on the formation of by-products. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:872 / 882
页数:11
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